Blue Frog Bar and Grill
676 N. La Salle Drive 312-943-8900
At this divey neighborhood hang, no cover-karaoke is on the agenda nearly every night of the week—with the exception of Mondays and Sundays.
GT Fish & Oyster
531 N. Wells St. 312-929-3501
This nautical-chic restaurant serves classics such as clam chowder and lobster rolls, but chef Giuseppe Tentori best shows off his skills with contemporary seafood plates featuring seasonal ingredients.
59 W. Hubbard St. 312-595-0800
The owners of Hub 51 down the block put a fun spin on a traditional French bistro with wine on tap and daily specials that range from loup de mer to coq au vin.
46 E. Superior St. 312-202-9141
At this garden-level family-run Mexican restaurant, chef Paco Lopez makes 18 molés on a rotating basis. A half dozen—with flavors ranging from cinnamon to almond to pumpkin—are featured during each dinner service.
435 N. Clark Street 312-610-4200
If whiskey, barbecue and a whole lot of country music is your idea of a fun time, look no further than this country-western bar and eatery.
18 W. Hubbard St. 312-955-8018
Chinatown restaurateur Tony Hu has plucked popular dishes from his fleet of Chinatown restaurants—think Szechuan tea-smoked duck and Peking-style dumplings—and assembled them all in one River North dining room.
The Boarding House
720 N. Wells St. 312-280-0720
Sommelier and former "Check, Please!" host Alpana Singh presides over this multi-floor wine bar and restaurant, where the decor—such as the chandelier made from thousands of wine glasses—is just as impressive as the bottle list.
339 N. Dearborn St. 312-755-9463
At this wine bar/restaurant/store hybrid, you find a new favorite by sampling a wine flight and then buy a bottle at the adjacent shop before heading home.
El Hefe Super Macho Taqueria
15 W. Hubbard St. 312-548-6841
Giant margaritas, novelty shots, sombreros and servers dancing on the bar are all par for the course at this over-the-top party bar.
Rockit Bar & Grill
22 W. Hubbard St. 312-645-6000
This reliable hangout has earned plenty of fans over the years, but it's especially well-known for its signature Rockit burger topped with brie, fried shallots, date aioli and served with truffle fries.
736 N. Clark St. 312-943-9700
This burger bar puts a decidedly adult spin on soda fountain favorites with a menu of boozy floats and milkshakes. Save room for the salty caramel shake spiked with Maker's Mark bourbon or an orange soda float with Grand Marnier and vanilla bean ice cream.